After graduating from Boca Raton Community High School, Carrabba became more serious about music and joined his first band, The Vacant Andys, and matriculated to Florida Atlantic University to study education.

Carrabba was a special education teacher prior to his success with Dashboard Confessional, often keeping a guitar in his office to write songs during downtime.

[4] In 2008, just as he was wrapping up work on the sixth Dashboard Confessional album, Carrabba's sister was in a serious car accident that put her in a coma for several months.

In 1998, while playing with the Vacant Andys, he filled in on guitar in New Found Glory, when regular guitarist Chad Gilbert was on tour with his other band, Shai Hulud.

It was announced on August 24, 2010, that Further Seems Forever would be reuniting with original vocalist Chris Carrabba with the release of a teaser video featuring rehearsal footage of the song "The Moon Is Down.

The album contains 10 tracks originally performed by artists that include R.E.M., Big Star, Guy Clark, Justin Townes Earle and the Replacements.